WHY WE CARE: Okay, so starting at the understanding that every collaboration between a brand and artist is ultimately about money, what's next? Some have called Kendrick Lamar's pitch work for Reebok awkward, unable to reconcile its "We the People" vibe with the trading of influence for sneaker sales. But even if that is the brand's ultimate goal, Lamar has managed to do it differently over the stretch of this two-year deal that started in 2014.

The Classic shoes he's hyping cost $75, incredibly low considering the eBay insanity that follows many a limited sneaker run. And he's used the advertising exposure to shine a light on young people in his hometown, and knows that cultural influence and brand popularity are most often not top-down. As he once told Fashionista, We can't run from the kids, period—and that's something that we always try to do in our own way. We throw the high cost on shoes and clothes and try to distract it from the kids, but they make the culture."

In this new spot, it's far from a flashy logofest, but a somber and determined moment of self-reflection.

"Greatness is my goal, but there's failure on the way/Full of insecurity, self-hate, and doubt/But what I can't control can't confine me/And what I can't do, can't stop me/This is how I express myself/Not how I follow others expectations/But how I stay true."

A sneaker ad, no doubt, but far from awkward.

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